


Truth or Dare

by orphan_account



Category: Supernatural
Genre: Alternate Universe - College/University, Alternate Universe - Human, Anal Fingering, Barebacking, Bottom Dean, Castiel and Jimmy Novak are Twins, Coming Untouched, Creampie, Dirty Talk, M/M, Multi, Multiple Orgasms, Oral Sex, Rough Oral Sex, Rough Sex, Sibling Incest, Size Kink, Smut, Threesome - M/M/M, Top Castiel, Top Jimmy, Truth or Dare
Language: English
Status: Completed
Published: 2017-09-12
Updated: 2017-09-12
Packaged: 2018-12-26 20:31:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,559
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12066456
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: Dean, Cas, and Jimmy are roommates, have been for years of college. One evening they decide to play truth or dare and things get a little out of hand.





	Truth or Dare

"Truth or dare? You guys have seriously never played that?"

Dean's incredulous tone didn't seem to bother the Novak twins as they shook their heads.

"We grew up in a _very_ conservative home," Jimmy admitted. 

"Our parents rarely let us out to hang out with _anyone_ \- let alone someone that would play a game that could possibly scar our delicate sensibilities."

Dean snorted, shaking his head. "I gotta admit - I don't envy you guys. Alright - so if you've never played - do you at least know _how_ it's played?"

The twins nodded in sync. It had taken Dean a few weeks to get used to that - the almost eerie way Cas and Jimmy moved together, as if they were the same person, rather than separate entities. He figured it had something to do with their sheltered upbringing, relying on each other and no one else. 

"So you go first then, Cas," Jimmy suggested. 

"Why me?"

"Alphabetical order," Dean said. "You have the first letter of the alphabet between the three of us. I'd say age, but you two --"

"I'm older," Jimmy said quickly. "By an hour."

"Really? I guess I always assumed it was-- I don't know, same time or something."

The twins shrugged and Cas cleared his throat, taking the bottle of beer Dean offered him. He took a hesitant sip before turning to his brother. "Truth or dare?"

"Dare -- You know pretty much every truth about me."

Cas's head tilted a little - a cute quirk that Dean had noticed he had. 

"I dare you to chug your beer."

Jimmy rolled his eyes and lifted the bottle to his mouth, wrapping his lips around the neck and tipping it back. Dean couldn't take his eyes away. Jimmy's Adam's apple bobbed hard, the audible gulps breaking up the silence of the room. His lips were sinful around the bottle, curled perfectly and teasing in just the right way. 

All too soon the bottle was empty. Jimmy dropped it from his lips with a sexy little smack and thunked it onto the table.

"My turn now?"

Dean's throat clicked when he tried to respond. He opted instead for a simple nod, not trusting himself to speak. 

"Alright, Dean. Truth or dare?"

"Truth," Dean whispered.

"How many people have you had sex with?"

"Total?" Dean clarified, his cheeks heating up. He could feel Cas staring at him, those bright blue eyes boring into his soul. 

"Yes."

Dean wet his lips. "I don't know. At least twenty."

"You're twenty-two," Cas said, and Dean cringed a little. 

"Well yeah-- Have sex more than once or twice a year, you know."

"When did you lose your virginity?" Cas asked. Dean grinned over at him and winked. 

"I already answered my truth. My turn. Cas-- Do you fantasize about anyone we know?"

The smile slipped from Cas' face. He looked down at the beer in hands for a moment, picking at the label. "Yes," he finally whispered. 

"Who?"

"I've already answered my truth, _Dean_."

Dean's grin widened at Cas' snarky tone and he nodded. "Touché. Your turn again."

“Dean. Truth or dare.”

“Dare.” 

“Take off your clothes.”

Dean nearly choked on the swig of beer he was taking. Jimmy laughed, leaning back in the chair he was in. He twined his fingers on his stomach, staring at Dean.

“Do we have a problem?” Cas asked, his big blue eyes shining with mischief as Dean struggled to formulate a response.

“All of them?” He finally squeaked, mentally kicking himself.

“All of them. That is, unless you concede and accept defeat of a _child’s_ game.”

Dean’s eyes narrowed. Of course Cas would say that – would play _that_ card. They both knew how competitive Dean could get. 

He stood up and unbuttoned his shirt, yanking it off with a little more force than necessary. The identical indigo gazes of his best friends were burning into him, making him painfully aware of the situation. 

A situation that _he_ was the master at. A slow smirk spread across Dean’s face, and he looked over at Cas. Stepping back so both could see him more easily, he began to strip – slower this time. Moving to a beat all his own, Dean pulled off his shirt and began to undo his jeans, his hips and ass swaying in a heartbeat rhythm. 

The quiet sigh from Jimmy’s direction drew his attention as he shimmied out of his boxers, his cock half hard just from the joy of teasing his highly attractive best friends.

“Good enough for you?” He asked.

Cas took a long drink from his bottle. “Yeah—“ He whispered when he’d swallowed. 

Dean sat down, his legs splayed open despite the stares from the twins. “My turn, right? Jimmy—Truth or dare?”

“T—Truth,” Jimmy stuttered.

“Do you like what you see?” Dean asked. He slid his bottom lip between his teeth, biting down teasingly as he watched Jimmy’s face redden more and more. 

“What? I—“

“Truth, Jimmy.”

“Fine—Yeah. You’re a good looking guy,” Jimmy mumbled. 

Dean’s grin widened and he nodded. 

“Cas, truth or dare?” Jimmy asked. 

“Dare.”

“Dare you to kiss Dean.”

“What?” Cas squeaked.

“Oh come on, I don’t have a disease,” Dean said, rolling his eyes. He grabbed Cas by the wrists and dragged him over, planting a wet kiss on his shocked, parted lips.

He sat back down and looked to Jimmy, eyebrows raised.

“The dare was for _Cas_ to kiss you – not stand there while you kissed him,” Jimmy argued, crossing his arms. Dean chuckled. He was painfully aware that his cock was hardening more and more each moment they spent together, and it had to be obvious to his friends at this point – though they put on an amazing show of not noticing.

“Fine,” Cas mumbled, pulling Dean out of his head. He rose and grabbed Dean’s face in a rough grip, pressing their lips together almost painfully hard. He loosened up quickly though, letting his tongue slip over Dean’s bottom lip. Instinctively, Dean wrapped his arms around Cas’ hips, pulling him a little closer in their kiss. 

They held it until Jimmy cleared his throat, pulling away in time to see him shift in his seat. 

“Good enough for you?” Cas asked, and Dean swore he could hear a hint of teasing _lust_ in his tone.

“Yeah, Cas. Perfect… Your turn.”

Cas smirked. “Truth or dare?”

“Truth.”

Cas’ eyes narrowed a little. “Are you a virgin, Jimmy?”

“You know the answer to that.”

“I don’t,” Dean said, crossing his arms. 

“But you’ve got a pretty good idea, right,” Jimmy asked.

Dean shrugged, saying nothing.

“Fine. No. I’m not a virgin.”

“What? You lost it?”

“Don’t look so shocked. We were sheltered, not prisoners.”

Dean grimaced. “Sorry, man—I didn’t mean—“

“We know,” Cas assured him. “For the record, I’m not one either. We were sheltered, so we understand your confusion.”

“Dean… Truth or dare.”

“Uh… Truth, I guess.”

“Who do you wanna fuck that’s in this room?”

“What?” 

Jimmy leaned forward, letting the tips of his fingers rest on Dean’s bare knee. “You’re hard. Now… Either the cold air and the white and black ambiance of a student apartment is sexy to you… Or you wanna fuck one of us. So… Do you?”

Dean swallowed hard. He looked down, wishing desperately for a way to hide his cock, hard against his hip. 

“I—Yeah, okay? But I won’t – I don’t wanna—“

“Why wouldn’t you?” Cas asked. “For all you know, one of us wants to fuck you too.”

“We’re friends. You guys are my best friends, I—“

“And friends turn into more all the time, Dean. So which one of us is it?”

Dean shook his head, staring at the bottle in front of him like it would answer all his questions. “Both,” he finally whispered.

“Both of us?” Cas asked softly. Dean nodded, fully expecting them to get up and leave. Instead, Cas just made a small noise and sat back. 

“Who’re you gonna ask, Dean?”

“Ask?”

“Truth or dare,” Jimmy clarified.

“Oh—Uh, Cas. Truth or dare?”

“Truth.”

“Do you wanna fuck someone in this room?”

Cas nodded slowly, his tongue darting out to wet his pink lips. “One of my biggest fantasies, actually,” he whispered.

Dean swallowed hard, his cock twitching at the heavy potential in Cas’ tone. 

“Jimmy—Truth or dare?” Cas asked, still staring at Dean.

“Dare.”

“I dare you to get naked.”

Dean’s head turned so quickly he feared he’d hurt his neck. Jimmy was already standing up, tugging his t-shirt over his head. He undid his belt next and fiddled with the zipper for a second, his eyes landing on Dean’s eager stare.

Dean's cock throbbed as Jimmy wiggled out of his pants. 

No underwear, Dean realized when Jimmy’s dick came into view, thick and perfect, half hard and getting harder each second. Dean made a pathetic noise, earning a laugh from the twins. Behind him, Cas nuzzled his neck. 

"Beautiful isn't he? Tastes just as good as he looks."

Dean blinked, turning to look at Cas. "What? You've--"

"What? Sucked my brother's cock? Of course I have. Did you think the experience we've had was with other people?"

Dean gulped. 

"But we've never had a threesome,” Cas continued, ignoring Dean’s shocked expression. 

“Gotta admit it's something we've always wanted to do," Jimmy said. He was sitting spread legged on the couch, completely nude as he stroked his cock to complete hardness.

"Me?" Dean whispered. He'd had a full, coherent question in his head - but his brain all but short circuited the moment he caught the glisten of precome dribbling down the smooth tip of Jimmy's cock.

"Yeah, you. If you think you can take him," Cas whispered.

"Can take anything if you're determined," Dean shot back.

"It's my turn, by the way," Jimmy said. "Dean? Truth or dare."

"What?" Dean blinked a few times. He shook his head. "Dare, I guess."

"Dare you to ride me. Take me as deep as you can."

Dean whimpered, pressing against the base of his cock. 

"Bare," Jimmy added after a moment.

Dean scrambled to his feet and into his bedroom in their apartment. He returned a few seconds later with a bottle of lube. 

"I'm gonna have to prep, guys I'm sorry -- it's been a few weeks--"

"Let me," Cas offered. He grabbed the bottle and shoved Dean onto the couch with a surprising strength. Together the twins shoved him exactly how they wanted him - his ass in the air where Cas began to lick and nip at it, and his head at Jimmy's chest, perfect angle for Jimmy to lean down and press a deep kiss to his mouth.

"You okay with this?"

"Yeah-- fuck, I-- was afraid you guys would be freaked out-- Cas!" He looked back and Cas grinned over his ass. He'd pressed one spit slicked finger into Dean's tight hole.

"Just warming you up. You can _see_ the size of Jimmy's cock."

Dean swallowed hard, glancing down at Jimmy's crotch. Cas wasn't wrong - it was even bigger up close.

"You admiring it or what?" Jimmy teased. 

"I-- I don't know if I can swallow this whole thing," Dean admitted. 

Jimmy grabbed his chin, letting his thumb prod Dean's lips before sliding in and prying open his teeth. 

"It'll fit. Know how I know?"

Dean shook his head. He slid his tongue over Jimmy's fingers, the salty taste of his sweat making his cock throb harder.

"I've watched you. Back when we lived in the dorm -- thought I was asleep, but I'd watch you choke yourself with that thick dildo of yours. Watch you choke on it until you cried, then shove it up your ass, fuck yourself until you made a mess on your stomach. You've never had a cock that big in real life, have you, Dean?"

"No," Dean whispered.

"You want one though, huh? Want a cock so big it hurts."

"Yes," Dean sobbed. He let Jimmy drag his head down, the clean, distinctly _male_ scent of Jimmy filling his nose. 

"Gonna go hard, Dean. Gonna take you apart, then Cas is gonna. You're gonna wanna cry when you sit tomorrow, understand me? Is that what you need?"

"Yes!"

"Say it," Jimmy instructed.

Dean swallowed thickly. "I need you to tear me apart. I need your cock-- both of your cocks, please, I-- Fuck!" Dean screamed against Jimmy's thigh when Cas pushed three lines fingers into him.

"Get used to it," Jimmy instructed, stroking Dean's hair. “That's nowhere near the size of my cock."

"Please--" Dean panted, his voice strained as Cas thrust his fingers.

"I need one of you to fuck me --"

"Little slut," Jimmy whispered, looking over Dean's body at Cas.

"You want first crack? You know he's gonna be a mess after I finish."

"Nah. You know I like it that way. Wanna trade?"

"Loosen him up a little more," Jimmy instructed, guiding Dean's head over his cock.

"Go on-- I know you wanna."

Without waiting for further command, Dean lifted Jimmy’s cock and wrapped his lips around the tip. He began to suck and lick what he could – admittedly not as much as he would have liked to. He let spit dribble from his mouth down the shaft of his cock, using his hand to make up for what his mouth couldn’t reach.

Jimmy groaned, arching his hips. His hand landed heavy on Dean's head, forcing him lower. Dean gagged, his stomach knotting at the knowledge that _that_ was going to be up his ass.

He pulled back, dragging in a shaky breath.

"It's so big, Jimmy."

"You bet your ass." Jimmy reached forward, grabbing a handful of Dean's ass and squeezing. 

Dean groaned, taking Jimmy's cock back in his mouth. His teeth grazed the sensitive skin of Jimmy's shaft, earning a quiet sigh of pleasure. "That's it, Dean-- I like it a little rough."

Dean let his teeth brush again, smirking as well as he could when Jimmy whimpered. 

Cas pulled his fingers free all too soon and stood.

"As good as I can get... Your turn." 

Dean scrambled up, straddling Jimmy's thighs.

"You sure about this?" Jimmy asked softly, sliding his hands over Dean's smooth, tense back.

Dean nodded. He rested his hands on the back of Jimmy's neck, playing with the short hairs there.

Cas took his hips at the same time Dean grabbed Jimmy's cock, lining it up to his hole. Together, the three pushed Dean down.

His head fell back, quiet huffs and whimpers slipping from his lips as Jimmy stretched him wider than he'd ever dreamed of feeling.

"So tight, Dean--" Jimmy panted.

Dean gasped Jimmy's name when the widest part of slipped past his rim. His legs shook under Jimmy's hands.

"It's okay if you come," Jimmy murmured, running the tip of his finger over the precome slick ridge of Dean's cock. 

"We'll still use your ass as long as we want."

Dean moaned brokenly, sinking down a little further on Jimmy's cock.

"It's too big-- I'm gonna-- I can't last."

"Then don't. You're gonna take it all the way up your ass. You need it, don't you?"

"Yes!" Dean panted.

Leaning back on Cas, he began to slide up and down what he could fit, his eyes rolling back when the muscles began to give. Jimmy's cock slipped deeper and deeper, forcing Dean open more. 

"That's it, Dean. Ride me, come on-- Let it happen," Jimmy instructed.

The moan that rose from Dean's throat was long and low, ending in a choked sob when another inch pushed past his stretched, aching rim. He felt like he was being split in two, a sick knot of pain and pleasure tying his stomach and closing off his throat when he tried to breathe. 

He dug his fingers into Jimmy's shoulders, the muscles in his thighs quivering as he rode him, Cas against his back to stabilize him. 

"Jimmy, I can't--"

"Come on, Dean, let go," Jimmy coaxed. Dean shouted through gritted teeth, slamming himself down on Jimmy. 

His cock began to spill, hot and thick on Jimmy's stomach as his ass slapped against Jimmy's thighs. 

Jimmy's back arched and he gasped. His fingers bit into Dean's hips as Dean's came untouched, his hole fluttering and clenching around the cock deep inside him. 

"Fuck-- You took it all, Dean," Cas whispered. He ran his finger around Dean's sensitive, stretched out rim. Dean gave a weak moan, his body shaking as he came down from his orgasm.

"My turn," Jimmy whispered, his voice full of promise - or threat. Dean wasn't sure, but he knew he wanted whatever it was. 

The twins settled him onto the couch on his back, Jimmy still deep in his ass. When he was comfortable, Jimmy pulled out and slammed back in, earning a surprised shout from Dean.

Cas took advantage, freeing his cock and sliding it into Dean's open mouth. He began to suck instinctively, pausing to moan around the shaft when Jimmy would drive into him. 

Back and forth, Dean's body was jerked between the twins. He felt dirty and used, his ass ached from Jimmy's thick cock and rough thrusts, and his throat was sore from the erratic pounding of Cas' hips.

"How's it feel, Dean?" Jimmy panted. Cas pulled back to let him answer, squeezing the base of his cock. Dean groaned, hooking his legs around Jimmy's waist.

"You're wrecking my asshole-- Fuck-- I'm never gonna be able to-- Fuck, Jimmy!" He arched his back, a second orgasm taking him by surprise. Jimmy held tight, fucking him through it. 

"That's it, Dean. Come on my cock. Slutty little size queen. Gonna ruin you for other guys."

Dean screamed against his hand, nodding in agreement.

Jimmy leaned forward, slamming hard into Dean. Cas met him halfway, kissing over Dean's half closed eyes. He gave a quiet, happy moan, reaching out to stroke Cas' cock.

"Gonna fill him up, brother?" Cas asked softly. Jimmy nodded. He grabbed Dean's thighs and pushed his legs open.

"You ready, Dean?"

When Dean only nodded, he slowed down. "Beg."

Dean moaned softly, his softening cock giving a tired twitch. 

"Fill up my ass, Jimmy please. Fuck me and wreck me-- make me need your cock to come. Fuck-- Please! You and Cas-- I need you to fucking use me, please, guys."

"Always, Dean," Cas whispered, pressing a soft kiss to his mouth. "You're ours, deal?"

"Yes," Dean whispered, repeating it quietly even as Jimmy groaned above him. He drove in, going still.

Dean could feel him throbbing, spilling hot and wet deep inside him. He gave a quiet moan, using his ass to milk the come from Jimmy's cock.

All too soon, Jimmy pulled out and traded with Cas.

"You're a mess, Dean. Gonna hurt tomorrow," Cas worried.

"Good," Dean whispered, smirking at him.

Cas slid in, gasping at the wet squelch of come and lube. Despite having been fucked wide by Jimmy, Dean could feel Cas' cock with almost painful clarity, and gave a quiet little moan.

"How's he feel, Cas?" Jimmy asked when Cas began to thrust.

"Amazing. He's swelling up so he's getting tighter-- I'm not gonna last."

"Don't need to. Think Dean's about to fall asleep." 

Dean nodded tiredly, trying his hardest to clamp down on Cas' cock. 

He didn't think he was doing much, but whatever it was was working - Cas began to grunt and thrust harder and quicker after just a few minutes.

"That's it. Fuck him, Cas. Wreck his ass."

"Cas!" Dean gasped, digging his short nails into Cas' ass.

"Fill me up, fuck me, use my ass, please!" He screamed. His back arched and he came a third time. He sobbed weakly, his cock twitching painfully as it dribbled the last of his come onto his belly. 

This seemed to be enough for Cas. He drove deep, some of Jimmy's come dribbling out around the base of his cock, and shouted Dean's name as he added to the mess inside him.

The three collapsed together on the couching in a sweating, panting heap. Dean broke the silence first, an anxious laugh bubbling up.

“What?” Jimmy asked, his voice slurred with exhaustion.

“We just fucked—“

“Mm… Glad you noticed,” Cas mumbled against Dean’s bare shoulder.

“What now?” Dean asked, fighting sleep. He needed to know.

“Now we should get cleaned up, and go to bed,” Jimmy suggested.

“Together?”

“Well—Cas I sleep together anyway. I think the bed’s big enough for one more.”

Dean snorted. “So that’s why you guys didn’t mind renting a two bedroom… So what are we?”

“Hm?”

“Like—Friends still or—“

“What do you wanna be, Dean?” Jimmy asked quietly. Their eyes met, and Dean smiled, turning enough to look at Cas for a moment.

“I—Really like you both. I have for years.”

“And we like you,” Cas assured him.

“So.. Maybe we should try being more than friends?”

“We could try a date. See how it goes. If it doesn’t feel right—We can do friends with benefits – or just friends,” Jimmy suggested.

Dean smiled and nodded. “That sounds like a plan.”

“No. What sounds like a plan is taking a shower before we’re glued together. I feel disgusting,” Cas complained, peeling himself off Dean’s back and standing.

Jimmy and Dean chuckled, following him up and into the shower.


End file.
